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Photo-mediated [1, 3]-Carbonyl shift of β-Ketocarbonyls

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Abstract An organic amine mediated photolytic [1,3]-benzoyl migration of β-benzoyl carbonyl compounds was reported. This migration was achieved by Norrish-Yang cyclization and retro-aldol reaction under black light (365 nm) or visible… Click to show full abstract

Abstract An organic amine mediated photolytic [1,3]-benzoyl migration of β-benzoyl carbonyl compounds was reported. This migration was achieved by Norrish-Yang cyclization and retro-aldol reaction under black light (365 nm) or visible light irradiation. This photolytic protocol provides an alternative approach to the synthesis of 1,5-dicarbonyl compounds. By chiral primary amine catalysis, a kinetic resolution was also developed to afford enantioenriched 1,5-dicarbonyls.

Keywords: photobiology; photo mediated; chemistry; shift ketocarbonyls; mediated carbonyl; carbonyl shift

Journal Title: Journal of Photochemistry and Photobiology A: Chemistry
Year Published: 2020

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